TWI392492B - 經取代磺醯胺，其製法，包括該經取代磺醯胺之組成物及其用途 - Google Patents
經取代磺醯胺，其製法，包括該經取代磺醯胺之組成物及其用途 Download PDFInfo
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- TWI392492B TWI392492B TW097108546A TW97108546A TWI392492B TW I392492 B TWI392492 B TW I392492B TW 097108546 A TW097108546 A TW 097108546A TW 97108546 A TW97108546 A TW 97108546A TW I392492 B TWI392492 B TW I392492B
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- Prior art keywords
- sulfonamide
- benzene
- bis
- benzamide
- ethyl
- Prior art date
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- 150000003456 sulfonamides Chemical class 0.000 title claims description 103
- 238000002360 preparation method Methods 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 229940124530 sulfonamide Drugs 0.000 claims description 98
- -1 4-( N,N-diethylaminoethoxy)benzyl Chemical group 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 48
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 25
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 208000010412 Glaucoma Diseases 0.000 claims description 6
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 239000000030 antiglaucoma agent Substances 0.000 claims description 4
- 150000003512 tertiary amines Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- BUGQZUIRDSIVRZ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-sulfamoylbenzamide Chemical compound CN(C)CCNC(=O)C1=CC=C(S(N)(=O)=O)C=C1 BUGQZUIRDSIVRZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000007344 nucleophilic reaction Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229940122072 Carbonic anhydrase inhibitor Drugs 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- LHTSZULGEREZGR-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-4-sulfamoylbenzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(=O)NCCN1CCOCC1 LHTSZULGEREZGR-UHFFFAOYSA-N 0.000 claims description 2
- YCEUIYKTVDZDRC-UHFFFAOYSA-N n-[3-(dipropylamino)propyl]-4-sulfamoylbenzamide Chemical compound CCCN(CCC)CCCNC(=O)C1=CC=C(S(N)(=O)=O)C=C1 YCEUIYKTVDZDRC-UHFFFAOYSA-N 0.000 claims description 2
- FPKHTEIUWUJTGY-UHFFFAOYSA-N n-[3-[butyl(ethyl)amino]propyl]-4-sulfamoylbenzamide Chemical compound CCCCN(CC)CCCNC(=O)C1=CC=C(S(N)(=O)=O)C=C1 FPKHTEIUWUJTGY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- RIDMSOMIFFTEJO-UHFFFAOYSA-N 2-sulfanylbenzamide Chemical compound NC(=O)C1=CC=CC=C1S RIDMSOMIFFTEJO-UHFFFAOYSA-N 0.000 claims 1
- OPBQRMZOKNTMDY-UHFFFAOYSA-N C1CCN(CC1)CCNC(=O)C2C=CC=CC2=S(=O)=O Chemical compound C1CCN(CC1)CCNC(=O)C2C=CC=CC2=S(=O)=O OPBQRMZOKNTMDY-UHFFFAOYSA-N 0.000 claims 1
- DGXOWMMXOZTMFH-UHFFFAOYSA-N CCN(CC)CCNC(=O)C1C=CC=CC1=S(=O)=O Chemical compound CCN(CC)CCNC(=O)C1C=CC=CC1=S(=O)=O DGXOWMMXOZTMFH-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- RGRVCIQMXWTJRO-UHFFFAOYSA-N n-(2-pyrrolidin-1-ylethyl)-4-sulfamoylbenzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(=O)NCCN1CCCC1 RGRVCIQMXWTJRO-UHFFFAOYSA-N 0.000 claims 1
- FPUJINAWQCKTQA-UHFFFAOYSA-N n-[2-[ethyl(propyl)amino]ethyl]-4-sulfamoylbenzamide Chemical compound CCCN(CC)CCNC(=O)C1=CC=C(S(N)(=O)=O)C=C1 FPUJINAWQCKTQA-UHFFFAOYSA-N 0.000 claims 1
- HNTHTZXWVDNAKA-UHFFFAOYSA-N n-[3-[ethyl(methyl)amino]propyl]-4-sulfamoylbenzamide Chemical compound CCN(C)CCCNC(=O)C1=CC=C(S(N)(=O)=O)C=C1 HNTHTZXWVDNAKA-UHFFFAOYSA-N 0.000 claims 1
- ABMSQUVUOUAVRV-UHFFFAOYSA-N n-[3-[ethyl(propyl)amino]propyl]-4-sulfamoylbenzamide Chemical compound CCCN(CC)CCCNC(=O)C1=CC=C(S(N)(=O)=O)C=C1 ABMSQUVUOUAVRV-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 32
- 239000007787 solid Substances 0.000 description 29
- 150000003863 ammonium salts Chemical class 0.000 description 21
- 235000002639 sodium chloride Nutrition 0.000 description 20
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000002671 adjuvant Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- RSIYXJOWRJIOEC-UHFFFAOYSA-N 4-amino-n-(3-morpholin-4-ylpropyl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NCCCN1CCOCC1 RSIYXJOWRJIOEC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000004410 intraocular pressure Effects 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
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- LFPUFCAIFUNCLI-UHFFFAOYSA-N 2-[4-(aminomethyl)phenoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=C(CN)C=C1 LFPUFCAIFUNCLI-UHFFFAOYSA-N 0.000 description 3
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 description 3
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
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- 239000003963 antioxidant agent Substances 0.000 description 1
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- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
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- 229960004324 betaxolol Drugs 0.000 description 1
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- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- RFWZESUMWJKKRN-UHFFFAOYSA-N dapiprazole Chemical compound CC1=CC=CC=C1N1CCN(CCC=2N3CCCCC3=NN=2)CC1 RFWZESUMWJKKRN-UHFFFAOYSA-N 0.000 description 1
- 229960002947 dapiprazole Drugs 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
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- 239000008103 glucose Substances 0.000 description 1
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- ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 1
- 229960003602 guanethidine Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- 238000007918 intramuscular administration Methods 0.000 description 1
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- GGXICVAJURFBLW-CEYXHVGTSA-N latanoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1 GGXICVAJURFBLW-CEYXHVGTSA-N 0.000 description 1
- 229960000831 levobunolol Drugs 0.000 description 1
- IXHBTMCLRNMKHZ-LBPRGKRZSA-N levobunolol Chemical compound O=C1CCCC2=C1C=CC=C2OC[C@@H](O)CNC(C)(C)C IXHBTMCLRNMKHZ-LBPRGKRZSA-N 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- NYIODHFKZFKMSU-UHFFFAOYSA-N n,n-bis(methylamino)ethanamine Chemical compound CCN(NC)NC NYIODHFKZFKMSU-UHFFFAOYSA-N 0.000 description 1
- OOYKEEROCQGXPH-UHFFFAOYSA-N n,n-diethyl-2-phenoxyethanamine Chemical compound CCN(CC)CCOC1=CC=CC=C1 OOYKEEROCQGXPH-UHFFFAOYSA-N 0.000 description 1
- ACWIBMMJPSBAFH-UHFFFAOYSA-N n-(2-piperidin-1-ylethyl)-4-sulfamoylbenzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(=O)NCCN1CCCCC1 ACWIBMMJPSBAFH-UHFFFAOYSA-N 0.000 description 1
- LAOOSMTXTNZTDT-UHFFFAOYSA-N n-(3-morpholin-4-ylpropyl)-4-sulfamoylbenzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(=O)NCCCN1CCOCC1 LAOOSMTXTNZTDT-UHFFFAOYSA-N 0.000 description 1
- NYXPGWZRJCJMMS-UHFFFAOYSA-N n-(3-pyrrolidin-1-ylpropyl)-4-sulfamoylbenzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(=O)NCCCN1CCCC1 NYXPGWZRJCJMMS-UHFFFAOYSA-N 0.000 description 1
- ZOCRHFLKYLDKQY-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-4-sulfamoylbenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(S(N)(=O)=O)C=C1 ZOCRHFLKYLDKQY-UHFFFAOYSA-N 0.000 description 1
- DEKYHUWUTSCYNY-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-4-sulfamoylbenzamide Chemical compound CN(C)CCCNC(=O)C1=CC=C(S(N)(=O)=O)C=C1 DEKYHUWUTSCYNY-UHFFFAOYSA-N 0.000 description 1
- IFMIJEOUWVXCDP-UHFFFAOYSA-N n-[3-[butyl(propyl)amino]propyl]-4-sulfamoylbenzamide Chemical compound CCCCN(CCC)CCCNC(=O)C1=CC=C(S(N)(=O)=O)C=C1 IFMIJEOUWVXCDP-UHFFFAOYSA-N 0.000 description 1
- 230000004493 normal intraocular pressure Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003650 oxygenase inhibitor Substances 0.000 description 1
- 230000001499 parasympathomimetic effect Effects 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000004634 pharmacological analysis method Methods 0.000 description 1
- 229960001416 pilocarpine Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 229940127230 sympathomimetic drug Drugs 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- 229960002368 travoprost Drugs 0.000 description 1
- MKPLKVHSHYCHOC-AHTXBMBWSA-N travoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)COC1=CC=CC(C(F)(F)F)=C1 MKPLKVHSHYCHOC-AHTXBMBWSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Ophthalmology & Optometry (AREA)
- Virology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SK54-2007A SK542007A3 (sk) | 2007-04-20 | 2007-04-20 | Substituované sulfónamidy, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200843730A TW200843730A (en) | 2008-11-16 |
| TWI392492B true TWI392492B (zh) | 2013-04-11 |
Family
ID=39671772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097108546A TWI392492B (zh) | 2007-04-20 | 2008-03-11 | 經取代磺醯胺，其製法，包括該經取代磺醯胺之組成物及其用途 |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US8193184B2 (es) |
| EP (1) | EP2142499B1 (es) |
| JP (1) | JP5492764B2 (es) |
| CN (1) | CN101663267A (es) |
| AR (1) | AR065966A1 (es) |
| AU (1) | AU2008241590B2 (es) |
| BR (1) | BRPI0809728A2 (es) |
| CA (1) | CA2684591C (es) |
| CL (1) | CL2008001109A1 (es) |
| DK (1) | DK2142499T3 (es) |
| ES (1) | ES2528284T3 (es) |
| HR (1) | HRP20141246T1 (es) |
| HU (1) | HUE024552T2 (es) |
| IL (1) | IL200952A0 (es) |
| JO (1) | JO3206B1 (es) |
| MA (1) | MA31364B1 (es) |
| MX (1) | MX2009010528A (es) |
| NZ (1) | NZ581302A (es) |
| PE (1) | PE20090807A1 (es) |
| PL (1) | PL2142499T3 (es) |
| PT (1) | PT2142499E (es) |
| RU (1) | RU2474574C2 (es) |
| SA (1) | SA08290238B1 (es) |
| SI (1) | SI2142499T1 (es) |
| SK (1) | SK542007A3 (es) |
| TN (1) | TN2009000421A1 (es) |
| TW (1) | TWI392492B (es) |
| UA (1) | UA99279C2 (es) |
| UY (1) | UY31028A1 (es) |
| WO (1) | WO2008130332A1 (es) |
| ZA (1) | ZA200906305B (es) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115141128B (zh) * | 2022-06-24 | 2024-09-13 | 沈阳药科大学 | 3-芳基-3-(磺胺苯甲酰胺基)丙(烯)酸衍生物及其制备方法及应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3502652A (en) * | 1965-01-19 | 1970-03-24 | Sandoz Ag | Basically substituted benzoic acid amides |
| JP2001162950A (ja) * | 1999-12-13 | 2001-06-19 | Fuji Photo Film Co Ltd | 感熱記録材料 |
| WO2006014134A1 (en) * | 2004-08-02 | 2006-02-09 | Astrazeneca Ab | Novel piperidine derivative for the treatment of depression |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2789938A (en) * | 1952-11-24 | 1957-04-23 | Merck & Co Inc | Method of producing a diuretic effect with p-carboxybenzenesulfonamide |
| GB1523631A (en) * | 1975-07-08 | 1978-09-06 | Leo Pharm Prod Ltd | Sulphonamide derivatives |
| EP0029090A3 (en) * | 1979-09-28 | 1981-07-01 | American Cyanamid Company | Sulfon amides containing a hindered phenol; stabilized composition containing a synthetic polymer and said sulfon amides |
| FR2504528A1 (fr) * | 1981-04-23 | 1982-10-29 | Choay Sa | Dialcoxy (2,4) benzenesulfonamides n-substitues |
| JPS5939867A (ja) * | 1982-08-27 | 1984-03-05 | Fuji Yakuhin Kogyo Kk | ２−クロロスルホニル−４−ｎ−置換スルフアミル−クロロベンゼンの製造法 |
| JPS6041071B2 (ja) * | 1983-07-28 | 1985-09-13 | ソシエテ・デチユ−デ・シヤンテイフイツク・エ・アンデユストリエル・ドウ・リル−ドウ−フランス | 安息香酸誘導体 |
| US4678855A (en) * | 1985-10-09 | 1987-07-07 | Merck & Co., Inc. | Substituted benzenesulfonamides |
| US4721809A (en) * | 1986-09-18 | 1988-01-26 | American Home Products Corporation | Alkylsulfonamido or perfluoroalkylsulfonamido benzenesulfonamides |
| JPH09510442A (ja) * | 1994-03-11 | 1997-10-21 | ファーマコペイア，インコーポレイテッド | スルホンアミド誘導体及びそれらの使用 |
| JP4139712B2 (ja) * | 2002-03-14 | 2008-08-27 | ライオン株式会社 | 漂白活性化剤及び漂白剤組成物 |
| EP2377569A1 (en) * | 2004-07-02 | 2011-10-19 | QLT Plug Delivery, Inc. | Treatment medium delivery device and methods for delivery of such treatment mediums to the eye using such a delivery device |
| WO2008071421A1 (en) * | 2006-12-15 | 2008-06-19 | Nicox S.A. | Nitrate esters of carbonic anhydrase inhibitors |
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2007
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| US3502652A (en) * | 1965-01-19 | 1970-03-24 | Sandoz Ag | Basically substituted benzoic acid amides |
| JP2001162950A (ja) * | 1999-12-13 | 2001-06-19 | Fuji Photo Film Co Ltd | 感熱記録材料 |
| WO2006014134A1 (en) * | 2004-08-02 | 2006-02-09 | Astrazeneca Ab | Novel piperidine derivative for the treatment of depression |
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